Two-Step Route toward Some Propellanes and Their Conversion into Stable Tricyclic Cations

DOI: 10.1021/jo00345a018

Source and publish data:

Journal of Organic Chemistry p. 984 - 988 (1982)

Update date:2022-08-03

Topics:

Authors:

Driessen, P. B. J.

Hogeveen, H.

Kruchten, E. M. G. A. van

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Article abstract of DOI:10.1021/jo00345a018

The synthesis of 1,4-tetramethylene(Dewar benzene) (2, a <4.2.2>propellane) and its conversion to the <4.3.2>propellanes 3 and 10 are described.Reaction of alcohol 10 with FSO3H/SO2ClF at low temperature (-135 deg C) yielded tricyclic cation 12, which rearranged at -75 deg C to a mixture of three isomeric cations.The structures and rearrangements of the cations were studied with 1H and 13C NMR spectroscopy and deuterium labeling.

Full text of DOI:10.1021/jo00345a018

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